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Dating Diaries: Lucy and Trevor

Lucy is a 27-year-old IT sales rep who lives in Parkdale. She describes her style as “random,” saying “I could be wearing a pink dress one day, and jeans, a T-shirt and Converse the next.” Lucy is “outgoing, caring, and straight to the point. I call out the obvious.” Lucy likes to “hit up sporting events — go Jays!” and host “creative parties,” as well as going bar hopping. She was single for five years, and says “I didn’t want to be in a serious relationship.”

For a while, I really enjoyed dating. First dates were always an excuse to grab a few drinks, meet new people and have a new bad-date story to rehash amongst friends. I was never picky about the place, who paid the bill, even the guys. But there was one rule: never date anyone from work. So when Trevor first hit on me at a company event last winter, I turned him down and thought nothing of it. Come Monday, my only concern was that he’d be awkward around me. He wasn’t. Two weeks later, at another company event, he hit on me again. This time, for some reason, I was feeling it.

We had planned to meet up the following Saturday afternoon. I realized that I had agreed to a weekend date and I never give up my weekend for a first date.

His plan was to take me to the CN Tower because I had told him I really wanted to stand on the glass floor. I was really excited to do something different and fun. But, I had dated so many lazy, unexciting men in this city — who were amazing at acting excited and then sending cliché bailing text messages — that when I woke up to a huge snowstorm I figured Trevor would cancel. When he called me to confirm our date instead, I got excited. Who knew that having the decency to call was such a turn-on?

We decided to kibosh the CN Tower idea and met up for a late lunch. I had originally told Trevor that I could only hang out during the day as I had a friend’s birthday party that night. We ate, we drank, we talked. We talked a lot. He was engaging, asking me a bunch of questions. We sat in that booth for hours. Before I knew it, the preshow for the hockey game was on.

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I went to use the bathroom and just as I sat back down, Trevor asked me if I wanted to go to the game. I was taken aback. He explained that we could try to grab tickets off a scalper as there weren’t that many people out due to the weather. The spontaneity was really hot.

The plan worked perfectly and the tickets were amazing. My excitement level was insane. I had never been so engaged in a date with someone before.

We watched the Leafs play one of their best games. If you watch the Leafs regularly, you know that those are few and far between. But I couldn’t help but watch Trevor. He talked stats with the father and son next to us and chatted up a couple to my left. He filled me in on Leafs-related information, while continuing to ask me questions. I couldn’t believe how comfortable I felt around him. He got me a shirt and we made it on the big screen.

I didn’t want the night to end. I had already broken some of my key rules, and was about to break one more: I asked if he wanted to come to my friend’s birthday. We got to the Bier Markt and I introduced him to everyone. Trevor bought my friend a round of shots and drinks, despite paying for everything all day, and joined us on the dance floor. We drunkenly slow danced and I blocked out everything around me. I knew right there and then, I never wanted him to let me go.

Lucy rates her date (out of 10): 10

The Dating Diaries are readers’ accounts of their best, worst and weirdest dates as-told-to the Star. Want to be a dating diarist? Email datingdiariescontact@gmail.com .

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